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Exploiting racemism enhanced organic room-temperature phosphorescence to demonstrate Wallach's rule in the lighting chiral chromophores.

ABSTRACT: The correlation between molecular packing structure and its room-temperature phosphorescence (RTP), hence rational promotion of the intensity, remains unclear. We herein present racemism enhanced RTP chiral chromophores by 2,2-bis-(diphenylphosphino)-1,1-napthalene (rac-BINAP) in comparison to its chiral counterparts. The result shows that rac-BINAP in crystal with denser density, consistent with a long standing Wallach's rule, exhibits deeper red RTP at 680?nm than that of the chiral counterparts. The cross packing between alternative R- and S- forms in rac-BINAP crystal significantly retards the bimolecular quenching pathway, triplet-triplet annihilation (TTA), and hence suppresses the non-radiative pathway, boosting the RTP intensity. The result extends the Wallach's rule to the fundamental difference in chiral-photophysics. In electroluminescence, rac-BINAP exhibits more balanced fluorescence versus phosphorescence intensity by comparison with that of photoluminescence, rendering a white-light emission. The result paves an avenue en route for white-light organic light emitting diodes via full exploitation of intrinsic fluorescence and phosphorescence.

SUBMITTER: Wu X

PROVIDER: S-EPMC7195388 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Exploiting racemism enhanced organic room-temperature phosphorescence to demonstrate Wallach's rule in the lighting chiral chromophores.

Wu Xiugang X Huang Chun-Ying CY Chen Deng-Gao DG Liu Denghui D Wu Chichi C Chou Keh-Jiunh KJ Zhang Bin B Wang Yafei Y Liu Yu Y Li Elise Y EY Zhu Weiguo W Chou Pi-Tai PT

Nature communications 20200501 1

The correlation between molecular packing structure and its room-temperature phosphorescence (RTP), hence rational promotion of the intensity, remains unclear. We herein present racemism enhanced RTP chiral chromophores by 2,2-bis-(diphenylphosphino)-1,1-napthalene (rac-BINAP) in comparison to its chiral counterparts. The result shows that rac-BINAP in crystal with denser density, consistent with a long standing Wallach's rule, exhibits deeper red RTP at 680 nm than that of the chiral counterpar ...[more]

PMID: 32358521

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Project description:Engineering the electronic excited state manifolds of organic molecules can give rise to various functional outcomes, including ambient triplet harvesting, that has received prodigious attention in the recent past. Herein, we introduce a modular, non-covalent approach to bias the entire excited state landscape of an organic molecule using tunable 'through-space charge-transfer' interactions with appropriate donors. Although charge-transfer (CT) donor-acceptor complexes have been extensively explored as functional and supramolecular motifs in the realm of soft organic materials, they could not imprint their potentiality in the field of luminescent materials, and it still remains as a challenge. Thus, in the present study, we investigate the modulation of the excited state emission characteristics of a simple pyromellitic diimide derivative on complexation with appropriate donor molecules of varying electronic characteristics to demonstrate the selective harvesting of emission from its locally excited (LE) and CT singlet and triplet states. Remarkably, co-crystallization of the pyromellitic diimide with heavy-atom substituted and electron-rich aromatic donors leads to an unprecedented ambient CT phosphorescence with impressive efficiency and notable lifetime. Further, gradual minimizing of the electron-donating strength of the donors from 1,4-diiodo-2,3,5,6-tetramethylbenzene (or 1,2-diiodo-3,4,5,6-tetramethylbenzene) to 1,2-diiodo-4,5-dimethylbenzene and 1-bromo-4-iodobenzene modulates the source of ambient phosphorescence emission from the 3CT excited state to 3LE excited state. Through comprehensive spectroscopic, theoretical studies, and single-crystal analyses, we elucidate the unparalleled role of intermolecular donor-acceptor interactions to toggle between the emissive excited states and stabilize the triplet excitons. We envisage that the present study will be able to provide new and innovative dimensions to the existing molecular designs employed for triplet harvesting.

Dataset Information

Exploiting racemism enhanced organic room-temperature phosphorescence to demonstrate Wallach's rule in the lighting chiral chromophores.

Publications

Exploiting racemism enhanced organic room-temperature phosphorescence to demonstrate Wallach's rule in the lighting chiral chromophores.

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